So Here’s the Thing…: Notes on Growing Up, Getting Older, and Trusting Your Gut(20)

I don’t think anyone would be able to make the connection between bagger at the grocery store and assistant to the president of the United States. But a lot of the skills and behaviors I developed doing odd jobs and grunt work have been useful. What will probably help regardless of your age and desired career: diligence, humility, and perspective. In every job, I tried to keep my head down, do good work, and own up to mistakes when I made them. I learned that not because someone had to tell me—doesn’t it seem a little obvious to see it written down?—but because all the people I admired worked in the same way. For all his rhetorical genius and charisma, Barack Obama wasn’t showy; he wasn’t constantly calibrating how an action would or would not make him appear. The same was true of all my previous bosses and mentors.

Of course mentors are wonderful. What I’m saying is that you shouldn’t be emulating them; you should be learning from them, taking what they can teach you, and applying it to your own life. Because not only are people different (duh), but the world changes rapidly, so what worked for me as a twenty-six-year-old in 2002 is not going to work the same for you as a twenty-six-year-old in 2019. For the first many years of my work life—note that this is different from “career”—offices were hierarchies. Lunch was never free, and neither was the coffee.

If you had an office, you were important. If you had a big office, you were even more important. And if you lived in a cubicle, your cube-mates were your only peers.1 I spoke freely to my cube-family, but in the hallways, when passing partners or other senior-level people, I didn’t strike up a conversation or ask about the weather—I cheerfully said, “Hello, Mr./Mrs. Whatever!” Yes—I only called them by their first names once they said it was OK.

In some ways, it was very restrictive. The boss could torture you with whatever he—and it was always a he—wanted. But in other ways at least you knew what the fuck was up—what the power structure was, whom you needed to impress (or at least pretend to be interested in). Back then, the path to promotion was very clear, and while it wasn’t kind to women, you knew what all your bosses had done to get where they were. In a post-corporate era, things can be tricky; when offices are open concept and leadership can be murky, it makes collaboration more fluid and easier, but it’s also hard to figure out what you need to do to get to the next level.2 Or what you need to do to avoid offending your coworkers. When I worked at Vice—which is famously “non-traditional”—if someone called me Ms. Mastromonaco I would have wondered if they needed to see a doctor. That’s not necessarily fair—there shouldn’t be anything wrong with assuming formality. But in that context—swarms of tattooed millennials in platform shoes talking about sex robots (for work!)—there definitely would be something off about showing up in a suit and addressing everyone like it’s your cotillion.3

All this is kind of abstract, I know. That’s both a good and a bad thing. This shift has taken place because of the internet, sure, but also because of all sorts of boundaries collapsing and re-forming. But before you get too overwhelmed, luckily there’s still the same, very tangible bottom line for most people: My primary goal with work has always been to make money to pay my bills. It’s awesome to be able to do something you love while earning enough money to avoid Top Ramen. But that’s a privilege, one that has to be earned. Everyone has the right to a roof over their heads, food on the table, health care, and dignity. (Well, in America, they don’t, but what I’m saying is that they should. Which is why I find myself drawn back to politics despite having vowed, when I left the White House, to never think about which tie a candidate should wear in a debate again.4) Not everyone has the right to work a glamorous job of their choosing. Especially not right out of college.

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When I was about to graduate from the University of Wisconsin, I knew that I wanted to go into politics and government. My internships with Bernie Sanders were some of the most eye-opening and exciting experiences I’d had that didn’t involve some kind of illegal substance or a jam-band soundtrack. So when the time came to apply for jobs, I sent faxes and letters to more than forty congressional offices, committees, political action committees, re-elects, campaign committees, and state offices.

Not one person responded to me.

I didn’t have the luxury of time, so by early August I had to take the plunge into the wild world of headhunters and try to find a place that would pay me to do something and, ideally, provide some health insurance.

Again, rounds of rejection.

What was I doing wrong?

Well. Despite all of what I just said about there being no right way to have a career, there are, actually, quite a few wrong ways to go about it. Starting with the interviews.

When I was applying for these non-political jobs initially, I have to admit that I wasn’t pumped about them. I was feeling dejected because the positions I wanted—and kind of felt I was destined for—weren’t having it. I can also be a little bit of a brat in general, and this was especially true in my teens and twenties. All this was showing in my interviews. I wasn’t enthusiastic; I didn’t have original answers to questions I could have easily prepared for. (Even if it’s true, the answer to “What most excites you about this position?” should never be “Not having to live at home with my parents.”)

You may not want the job, but you may need the job. It doesn’t have to be your dream, but you can psych yourself up on its possible positive outcomes: paying rent, getting “professional experience,” paying off college loans, putting away some savings (I used my overtime at the job I eventually did get to go to Japan!), learning new software, living in a new city, meeting new people. Try to sell yourself on the upsides, so you can go in with some unforced positivity. And never act like a position is beneath you, even if it is. The moral of my story is that I wasn’t being particularly enthusiastic in my interviews—I wasn’t acting like real estate paralegaling was my passion, because it wasn’t. Only after a few awkward “We’ll call you”s did I realize that I was interviewing with people who were passionate about it. Well, maybe not about paralegaling, per se, but the career for which being a paralegal is an important first step. It’s pretty easy to offend someone that way. It would be like if someone showed up for an interview to work at a family restaurant and said, “I mean, I don’t really care about food. Or families.”